Find flights
When to book
FAQs & Tips
Direct Flights
Airlines
Deals

Find cheap flights from Caribbean to Chicago from $46

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 5/21. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
dom. 6/2
dom. 6/9

Search hundreds of travel sites at once for deals on flights to Chicago

In the last 7 days travelers have searched 43,740,974 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Good to know

Low season

March

High season

July

Cheapest flight

$46
Best time to beat the crowds but there is an average 27% increase in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from San Juan Airport to Chicago O'Hare Airport

FAQs for booking flights from Caribbean to Chicago

  • How does KAYAK find such low prices on flights from Caribbean to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Caribbean to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Caribbean to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Caribbean is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Caribbean to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Caribbean with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly non-stop from Caribbean to Chicago?

Find which airlines fly direct from Caribbean to Chicago, which days they fly and book direct flights.

Nonstop departures

Caribbean to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

See more direct flights

Nonstop returns

Chicago to Caribbean

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

See more direct flights
See more direct flights

Top 5 airlines serving from Caribbean to Chicago

 
Need help choosing which airline to fly with from Caribbean to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10858 reviews
8.6Crew
8.0Entertainment
7.4Food
7.9Comfort
8.2Boarding
Airline reviews

The crew were very welcoming and helpful. I just wish economy had a bit more leg room. My knees were constantly hitting the chair in front of me.

8.0 ExcellentAshlee, May 2024KIN - ATL
Read more about Delta reviews

The crew were very welcoming and helpful. I just wish economy had a bit more leg room. My knees were constantly hitting the chair in front of me.

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

We were delayed an hour leaving Munich (No fault of the crew). They kept us posted on the status so we knew what was going on, but as a result we missed our connection in Chicago and the communication on connecting flights was pretty poor as we disembarked. It was already stressful and some of that could have been reduced by better communications about where to find transfers, etc.

One problem, but a serious one - the plane is built with electric windows that tint dark to reduce light. Sitting next to the window is VERY UNCOMFORTABLE as it emits so much HEAT in the face when tinted.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

Wifi wasn't working on one of the UA flights after boarding.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Crew was not very helpful. They forgot to serve me coffee and had to wait for a long time.It looked as if they were not very happy with what they were doing.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

The plane was old and in new of a cleaning up and renovating on the interior. Seats and carpets were very worn and dirty looking. Cushioning on the seats was broken down and not as comfortable as newer jet seats. Food was a little below average but okay. Staff were friendly and hard working but did not pick up debris or food they spilled when collecting from the customers. But they were very helpful and professional.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

lounge was the highlight - seats weren't that comfortable - it was a full flight but no complaints

I paid for WiFi, but it (WiFi) was very very slow, will never take again! Impossible open Utube 😤😤😤

I had no legroom, although I paid for extra legroom. I could barely put my bag in front of my feet and under the seat. The Wi-Fi was horrible. In fact the flight attendant said that they had to reboot it and see if it was going to work and never did.

The seat are terrible. Don’t even think of sleeping on a Spirit flight. The kids that run the plane aka flight attendants are pretty rude and straight forward. They get the job done but without class.

I had a death in my family and booked my flight on Spirit. My flight was cancelled the morning of my flight, no explanation, no help to rebook, nobody to talk to. The next available flight was 2days later !!!! Terrible airline, will NEVER fly with them again!

They took a horrible route with a lot of turbulence and I eneded up getting sick. Even if the flight takes longer. Don't put people life at risk just to get to the airport on time.

Every thing was fine ,low price,easy on time ,clean, good staff, really no issues

Had to board plan 2x due to lack of security check after 1st boarding

Miserable. The crew was rude, the flight was delayed 5 hours for mechanical reasons and then “weather” even though other planes were leaving.

They kept Changing the flight times. It was delayed several times and at one point it was supposed to depart at 3.40am! At which point we ended up staying overnight and booked long a separate United flight for early morning departure. The spirit flight then got moved up and left at 1.30 in the morning when it was supposed to leave at 9.40pm the night before.

Flight was delayed...not horribly late. Just before push back engine shut down for a quick replacement item that took about five minutes. After that, everything was smooth and the pilot was able to make up time in the air so that our arrival time was not too far off the original anticipated arrival time.

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Book cheap flights from Caribbean to Chicago

Recent round-trip flight deals

5/29mié.
1 stopSpirit Airlines
13h 48mSJU-ORD
6/3lun.
1 stopSpirit Airlines
6h 41mORD-SJU
$132
6/5mié.
nonstopSpirit Airlines
5h 11mSJU-ORD
6/11mar.
1 stopSpirit Airlines
15h 12mORD-SJU
$141
5/14mar.
1 stopFrontier
21h 35mSJU-ORD
5/17vie.
1 stopFrontier
26h 20mORD-SJU
$205
5/12dom.
1 stopFrontier
21h 35mSJU-ORD
5/17vie.
1 stopFrontier
15h 51mORD-SJU
$215
5/15mié.
nonstopAmerican Airlines
4h 30mMBJ-ORD
9/2lun.
nonstopAmerican Airlines
4h 00mORD-MBJ
$357
5/25sáb.
nonstopUnited Airlines
4h 24mMBJ-ORD
6/22sáb.
1 stopUnited Airlines
17h 21mORD-MBJ
$362
5/15mié.
nonstopAmerican Airlines
4h 30mMBJ-ORD
9/2lun.
nonstopAmerican Airlines
4h 00mORD-MBJ
$367
6/27jue.
2 stopsDelta
7h 38mNAS-ORD
7/2mar.
1 stopDelta
4h 55mORD-NAS
$424
9/20vie.
1 stopDelta
19h 37mSDQ-ORD
9/24mar.
1 stopDelta
6h 23mORD-SDQ
$433
5/25sáb.
nonstopUnited Airlines
4h 24mMBJ-ORD
5/31vie.
nonstopUnited Airlines
4h 00mORD-MBJ
$521

Search by stops

Search by airline

Search by price

Recent one-way flight deals

5/21mar.
1 stopSpirit Airlines
10h 24mSJU-ORD
$46
5/21mar.
1 stopSpirit Airlines
13h 48mSJU-ORD
$49
5/15mié.
nonstopFrontier
5h 29mPUJ-ORD
$100
5/8mié.
1 stopFrontier
9h 44mSJU-MDW
$109
6/9dom.
1 stopAmerican Airlines
13h 35mSJU-ORD
$118
5/14mar.
1 stopAmerican Airlines
8h 50mSJU-ORD
$119
5/18sáb.
2 stopsDelta
19h 50mSDQ-ORD
$208
5/18sáb.
2 stopsDelta
19h 36mSDQ-MDW
$208
6/13jue.
1 stopUnited Airlines
17h 13mMBJ-ORD
$231
6/1sáb.
nonstopUnited Airlines
4h 24mMBJ-ORD
$241

Search by stops

Search by airline

Search by price

Last minute flights from Caribbean to Chicago

Last minute flight, train and bus deals

5/3vie.
nonstopFrontier
5h 28mPUJ-ORD
5/6lun.
nonstopFrontier
4h 41mORD-PUJ
$182
5/7mar.
multi-stopSpirit Airlines
13h 55mSJU-ORD
6/25mar.
multi-stopSpirit Airlines
10h 29mORD-SJU
$190
5/4sáb.
nonstopSpirit Airlines
5h 19mSJU-ORD
5/6lun.
multi-stopSpirit Airlines
12h 38mORD-SJU
$192
5/3vie.
multi-stopFrontier
21h 34mSJU-ORD
5/18sáb.
multi-stopFrontier
7h 13mORD-SJU
$252
5/3vie.
multi-stopAmerican Airlines
17h 20mSJU-ORD
5/5dom.
multi-stopAmerican Airlines
6h 40mORD-SJU
$265
5/7mar.
multi-stopAmerican Airlines
9h 40mSJU-ORD
5/15mié.
multi-stopAmerican Airlines
10h 50mORD-SJU
$274
5/4sáb.
nonstopUnited Airlines
4h 24mMBJ-ORD
5/28mar.
multi-stopUnited Airlines
17h 21mORD-MBJ
$362
5/3vie.
multi-stopUnited Airlines
9h 31mSJU-ORD
5/7mar.
nonstopUnited Airlines
4h 50mORD-SJU
$362
5/8mié.
multi-stopDelta
18h 25mSDQ-MDW
5/11sáb.
multi-stopDelta
20h 20mMDW-SDQ
$470
5/6lun.
multi-stopDelta
17h 50mSDQ-ORD
5/15mié.
multi-stopDelta
15h 20mORD-SDQ
$495

Search by stops

Search by airline

Search by price